4-Formylphenylboronic acid

Base Information

• Chemical Name: 4-Formylphenylboronic acid
• CAS No.: 87199-17-5
• Deprecated CAS: 2599159-62-1
• Molecular Formula: C7H7BO3
• Molecular Weight: 149.942
• Hs Code.: 29163990
• European Community (EC) Number: 438-670-5
• UNII: Z4V1TO2DWR
• DSSTox Substance ID: DTXSID6074887
• Nikkaji Number: J565.950G
• Wikipedia: 4-Formylphenylboronic_acid
• Wikidata: Q28101340
• ChEMBL ID: CHEMBL140254
• Mol file: 87199-17-5.mol

Synonyms:4-formylphenylboronic acid;P-formylphenylboronic acid

Chemical Property of 4-Formylphenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 237-242 °C(lit.)
• Boiling Point: 347.584 °C at 760 mmHg
• PKA: 7.34±0.10(Predicted)
• Flash Point: 164.013 °C
• PSA: 57.53000
• Density: 1.244 g/cm³
• LogP: -0.82110
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Solubility.: <10g/l
• Water Solubility.: Slightly Soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 150.0488242
• Heavy Atom Count: 11
• Complexity: 130

Purity/Quality:

>98% ^*data from raw suppliers

4-Formylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 22-26-36/37/39-45-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C=O)(O)O
• Uses: suzuki reaction 4-Formylbenzeneboronic acid acts as a reagent used for Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water, copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids, triethylamine-catalyzed three-component Hantzsch condensations, copper-catalyzed nitrations, oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta, palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides, palladium-catalyzed aerobic oxidative cross-coupling reactions. It acts as a reagent used in preparation of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells, a novel protein synthesis inhibitor active against Gram-positive bacteria. 4-Formylphenylboronic acid is a substrate for Suzuki cross-coupling reactions and it can be used as a reagent for:Palladium-catalyzed Suzuki-Miyaura cross-coupling in water. Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides. Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids. Triethylamine-catalyzed three-component Hantzsch condensations. Copper-catalyzed nitrations. Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta. Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides. Palladium-catalyzed aerobic oxidative cross-coupling reactions. The synthesis of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells.The synthesis of a novel protein synthesis inhibitor active against Gram-positive bacteria.The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene.A rhodium-catalyzed cyclization, converting 1,5-enynes to cyclopentenes and spiro-cyclopentenes.

Technology Process of 4-Formylphenylboronic acid

There total 34 articles about 4-Formylphenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

potassium 4-formylphenyltrifluoroborate → 4-formylphenylboronic acid, (87199-17-5)

Guidance literature:

With iron(III) chloride; water; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2011.09.140

Reference yield: 90.0%

p-hydroxymethylphenylboronic acid (59016-93-2) → 4-formylphenylboronic acid, (87199-17-5)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1002/anie.200906710

Reference yield: 88.0%

4-allylphenylboronic acid (186497-79-0) → 4-formylphenylboronic acid, (87199-17-5)

Guidance literature:

With Triethoxysilane; iron(III) chloride; In methanol; for 12h; Reflux;

upstream raw materials:

4-bromomethylphenylboronic acid

2-(4-bromophenyl)-1,3-dioxane

p-bromobenzaldehyde 1,3-dioxolane

Triisopropyl borate

Downstream raw materials:

dihydroxy-[4-(2-nitro-vinyl)-phenyl]-borane

4-(2-Methoxycarbonyl-phenyl)-Benzaldehyde

2-<2-(4-formylbenzoyl)phenylamino>-3-<4-<2-(5-methyl-2-phenyloxazol-4-yl)ethoxy>phenyl>propionic acid methyl ester

Refernces

• 1、 Ju, Huiyeong,Taniguchi, Aya,Kikukawa, Kaoru,Horita, Hiroki,Ikeda, Mari,Kuwahara, Shunsuke,Habata, Yoichi. "Argentivorous Molecules with Chromophores in Side Arms: Silver Ion-Induced Turn on and Turn off of Fluorescence". supporting information. p. 9141 - 9147. Retrieved 2021/06/28.
• 2、 Fan, Chenrui,Wu, Qixu,Zhu, Chengfeng,Wu, Xiang,Li, Yougui,Luo, Yunfei,He, Jian-Bo. "Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions". supporting information. p. 8888 - 8892. Retrieved 2019/10/14.